A Practical Protocol for the Conjugation of Various Amino Acids to Protoporphyrin IX

Ksenia Maximova; Sabina Pisarek; Dorota Gryko

doi:10.1055/s-0032-1318486

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(8): 1099-1105
DOI: 10.1055/s-0032-1318486

paper

A Practical Protocol for the Conjugation of Various Amino Acids to Protoporphyrin IX

Ksenia Maximova

Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 eMail: dorota.gryko@icho.edu.pl

,

Sabina Pisarek

Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 eMail: dorota.gryko@icho.edu.pl

,

Dorota Gryko*

Institute of Organic Chemistry, PAS, Kasprzaka 44/52, 01-224 Warsaw, Poland Fax: +48(22)6326681 eMail: dorota.gryko@icho.edu.pl

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Abstract

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Abstract

An effective and reliable method was developed for the synthesis of protoporphyrin IX-derived amides. The reaction of protoporphyrin IX with an amino acid [l-leucine, l-valine, l-lysine, l-aspartic acid (Asp), l-glutamic acid (Glu), glycine, or 6-aminohexanoic acid] or a short peptide (Asp-Glu) as an amine counterpart in the presence of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate and 1H-1,2,3-benzotriazol-1-ol gave the desired diamides in excellent yields.

Key words

porphyrins - amides - amino acids - peptides - esters - hydrolysis

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